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Dear Uncle Mat

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I fucked up again. My friend has this crush on a girl who bartends at our favorite bar. Last night she finally got the nerve to ask her out and they made a date. Later the bartender and I were hanging out at an after-hours party at my place and we totally did it. I don’t know why I do these things. I don’t even really like her. I was just drunk and horny I guess. My friend called today to tell me how excited she is about their date — tonight! I feel like shit, but don’t think telling her is a good idea. It could be a bad date anyways, and then I would only be pissing her off for no reason. I don’t think I should tell her. At least not now. Is this OK? If I do tell her, when should I? I am a total ass. Also it is important to mention that my friend is totally bigger than me and could kick my ass. So tell me, what now Mr. Know It All?

— Oops, I did it again.

Dear Oops,

You know flattery will get you everywhere. Seriously. And since when did lesbians start quoting Britney Spears?

You should have told her before you wrote me this letter. Telling her is going to suck and she may hate you. This is a hazard of whoring around. You did mention that you “did it again.” How often do you do it? I am referring to making bad sex decisions. Reflect on this and ask yourself why you would sleep with the object of your friend’s affection. You were drunk? That is a piss-poor excuse, young lady. I strongly recommend drinking less. Especially if it is a recurring element in your escapades. Drunk sex is the leading cause of pretty much everything that goes wrong with sex, including — but not limited to — STDs, unintentional pregnancy, general embarrassment, and getting your ass kicked. Please be careful.

Apparently you didn’t tell your friend the morning after or before her date, so now there are alternatives for timing the disclosure. Ask how the date went and find out how much she likes this other woman. With any luck she isn’t as easy as you and the bartender has enough sense and morals not to screw two friends in the same 24 hours. If the date was in fact a bomb, I suppose you could just let it go, but that might come back to bite you in the ass later. This happened at an after-hours party, so I am betting other people know or possibly suspect. Another person might tell your friend. You will then be a liar and this third party might make you sound even worse (though I am not sure how). If the bartender was a bitch or displayed some unforgivable habit, your friend might enjoy knowing that you suffered the embarrassment of shagging her. This will really depend on the nature of your friendship and your friend’s general disposition. Is she your BFF or just a drinking pal? Assuming she knows of your past feats, does she find them amusing, tragic, or distasteful?

If your friend had a wonderful time and is starstruck, you have a bigger problem. Start by talking to the date. How does she feel about your friend? About your little mishap? What is her reaction to the idea of you disclosing the mutual indiscretion? None of these answers change the fact that you should tell your friend. You should want to know if this woman has good intentions toward your friend. A good friend would tell someone if his or her new infatuation is a slut. Especially if it is from first-hand experience. The sooner the better.

I hope you don’t lose your friend, but she deserves a good friend. Be honest. Set yourself some boundaries. Avoid mixing booze and loose women. Avoid being a loose woman. Follow your friend’s example and try dating a chick before you sleep with her. Not that bars aren’t fun, but you can also meet ladies at other places. Knowing and remembering simple facts like last names, hobbies, and favorite books will actually make the sex better — most of the time.